Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Author(s)

Medina, Rebeca P. ^[1] ; Araujo, Angela R. ^[1] ; Batista Jr, Joao M. ; Cardoso, Carmen L. ^[2] ; Seidl, Claudia ^[2] ; Vilela, Adriana F. L. ^[2] ; Domingos, V, Helori ; Costa-Lotufo, V, Leticia ; Andersen, Raymond J. ^{[3, 4]} ; Silva, Dulce H. S. ^[1]

Affiliation

^[1] UNESP Univ Estadual Paulista, Nucleo Bioensaios Biossintese & Ecofisiol Prod Na, Dept Quim Organ, Inst Quim, BR-14801970 Araraquara, SP - Brazil

^[2] Univ Sao Paulo, Grp Cromatog Bioafinidade & Prod Nat, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, BR-14040901 Ribeirao Preto, SP - Brazil

^[3] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1 - Canada

^[4] Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1 - Canada

• Document type: Journal article
• Source: SCIENTIFIC REPORTS; v. 9, AUG 23 2019.
• Web of Science Citations: 1

Abstract

A chemical study of the EtOAc extract of Nemania bipapillata (AT-05), an endophytic fungus isolated from the marine red alga Asparagopsis taxiformis - Falkenbergia stage, led to the isolation of five new botryane sesquiterpenes, including the diastereomeric pair (+)-(2R, 4S, 5R, 8S)-(1) and (+)-(2R, 4R, 5R, 8S)-4-deacetyl-5-hydroxy-botryenalol (2), (+)-(2R, 4S, 5R, 8R)-4-deacetyl-botryenalol (3), one pair of diastereomeric botryane norsesquiterpenes bearing an unprecedented degraded carbon skeleton, (+)-(2R, 4R, 8R)-(4) and (+)-(2R, 4S, 8S)-(5), which were named nemenonediol A and nemenonediol B, respectively, in addition to the known 4 beta-acetoxy-9 beta, 10 beta, 15 alpha-trihydroxyprobotrydial (6). Their structures were elucidated using 1D and 2D NMR, HRESIMS and comparison with literature data of similar known compounds. The absolute configurations of 2, 3 and 4 were deduced by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, while those of 1 and 5 were assigned from vibrational circular dichroism (VCD) data. Compound 4 weakly inhibited acetylcholinesterase, whereas compound 1 inhibited both acetylcholinesterase and butyrylcholinesterase. Compounds 1, 3, 5 and 6 were tested against two carcinoma cell lines (MCF-7 and HCT-116), but showed no significant citotoxicity at tested concentrations (IC50 > 50 mu M). (AU)

• FAPESP's process: 13/01710-1 - Enzyme ligand: new models of screening
• Grantee: Quezia Bezerra Cass
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 14/50926-0 - INCT 2014: biodiversity and natural products
• Grantee: Vanderlan da Silva Bolzani
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• FAPESP's process: 15/17177-6 - Integrative approach on the sustainable prospection of marine natural products: from diversity to anticancer compounds
• Grantee: Leticia Veras Costa Lotufo
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC